105243-14-9

Upstream product

• 936650-20-3 (11R,12R,13R,14R)-11,14-bis(benzyloxy)tetracosane-12,13-diol 
• 60902-45-6 nonyltriphenylphosphonium bromide 
• 101685-77-2 Formic acid (E)-(1R,2R)-2-benzyloxy-1-(5-methyl-hexyl)-dodec-3-enyl ester 
• 120663-14-1 (7R,8R)-8-benzyloxy-7-hydroxy-2-methyl-9-octadecene 
• 101685-73-8 4-C-(5-methylhexyl)-3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-tetrofuranose 
• 101685-74-9 4-C-(5-methylhexyl)-3-O-benzyl-D-xylo-tetrofuranose 
• 101685-71-6 4-C-(5-methyl-1-hexenyl)-1,2-O-isopropylidene-α-D-xylo-tetrofuranose 
• 101685-72-7 4-C-(5-methylhexyl)-1,2-O-isopropylidene-α-D-xylo-tetrofuranose 
• 70240-41-4 4-methyl-1-pentyltriphenylphopshonium bromide 
• 85514-80-3 (R)-2-(benzyloxy)dodecanal 
• 98-59-9 p-toluenesulfonyl chloride 
• 936650-19-0 (4S,5S)-4,5-bis((R)-1-hydroxyundec-1-yl)-2,2-dimethyl-1,3-dioxolane 
• 936650-18-9 (4R,5R)-4,5-diundecanoyl-2,2-dimethyl-1,3-dioxolane 
• 936650-22-5 (4R,5R)-5-(benzyloxy)-4-(p-toluenesulfonyloxy)pentadec-1-ene 

Relevant academic research and scientific papers

Enantiodivergent synthesis of both enantiomers of gypsy moth pheromone disparlure

(Chemical Equation Presented) Enantiodivergent synthesis of both (-)- and (+)-disparlure, a bioactive pheromone, possessing a cis-epoxide has been accomplished. The key step involves the cross metathesis of a chiral homoallylic alcohol derived from L-(+)-tartaric acid.

STEREOSELECTIVE SYNTHESIS OF BOTH ENANTIOMERS OF DISPARLURE, THE SEX PHEROMONE OF THE GYPSY MOTH, FROM D-GLUCOSE

1,2-O-Isopropylidene-α-D-xylopentodialdo-1,4-furanose readily avalaible from D-glucose was transformed in two Wittig reactions and glycol cleavage into a (Z) and (E) mixture of (7R,8R)-8-benzyloxy-7-hydroxy-2-methyl-9-octadecenes.From this chiral synthon both enantiomers of disparlure, (7R,8S)-(+)- and (7S,8R)-(-)-7,8-epoxy-2-methyloctadecane were obtained in four and three steps, respectively.